


The Bet

by badcircuit



Series: Things that Never Happened [5]
Category: Actor RPF, American Actor RPF
Genre: Anal Fingering, Ass Play, F/M, Feminization, Oral Sex, Pegging
Language: English
Status: Completed
Published: 2014-08-01
Updated: 2014-08-01
Packaged: 2018-02-11 09:36:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,105
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2063127
Author URL: https://archiveofourown.org/users/badcircuit/pseuds/badcircuit
Summary: <blockquote class="userstuff">
              <p>Based on a prompt on the Jeremy Renner Frustration tumblr where “Jeremy loses a bet and as a result he must dress in drag for the amusement and titillation of his lady.”  Of course, if I’m writing it, you know it’s not going to be as simple as that sounds. </p><p>Bless my beta queen, disturbedbydesign, who gets me.</p>
            </blockquote>





	The Bet

**Author's Note:**

  * For [disturbedbydesign](https://archiveofourown.org/users/disturbedbydesign/gifts).



The bet was simple. All he had to do was go one week without a cigarette. He could have done it; he can be extremely disciplined when he has to be. He fucked up on purpose without even knowing what I'd claim for my prize.  

Granted, my prizes are things of beauty.

I'm very creative and extremely dirty. My prizes push his boundaries in the best ways. He may lose our bets but he's never really the loser. No, the way we play, everyone wins.

He tries to look sorry when he comes to confess his slip-up, bless his filthy heart. He may be an actor but there are some things he can't hide from me, things that are nowhere near as obvious as the growing bulge in his jeans when I tsk him.

I sigh heavily. "All you had to do was this one thing."

"I know. I'm sorry." He gives me the puppy dog eyes and I nearly laugh. The bastard.

I put down the apple I'd been munching and give him a long stare, from his motorcycle helmet hair down to his favorite old boots. "No you're not but you will be."

"Ooooh, scary," he says, hand to his chest dramatically.

"You're just making it worse for yourself." I take up my apple again and take a vicious bite. He should know better than to taunt me by now.

I wait a couple of days until I have all of my shit ready, savoring his increasing agitation. When he comes home from the gym, sweaty and relaxed, I spring it on him.

I meet him at the door, hands on my hips. "Go shower. I want my prize now."

He doesn't say a word but he straightens up like he's been poked with a cattle prod and drops his keys, phone, and water bottle like they're on fire. "Yeah, ok."

He's so cute when he's blindsided.

I'm sitting on the bed when he comes out of the bathroom, the towel he's got wrapped around his hips clinging for dear life as he rubs his hair dry. When he notices me there, smiling oh so pleasantly, he jumps and chuckles.   "Hey."

"Hey. Come over here."

He does and when he sees what's lying next to me on the bed, he tries to take a step back but I grab the towel so that he can't. "Regretting that smoke now, huh?"

He shakes his head, still eyeing the stuff on the bed. "Fuck...seriously?"

"Are you not honoring this bet?" There's a word he can say to call it off and for a moment, I think he just might.

He inhales through his nose and blows it out slowly. His rising cock bumps my wrist and I let the towel drop to the floor. "I'm honoring it. You're one diabolical bitch, you know that?"

I laugh delightedly; he's such an adorable grump.

I hold out the panties first and he snatches them, holding them up between finger and thumb, frowning fiercely at them. "You like them well enough when I wear them," I say.

"Because you look good in red lace," he grumbles.

When he hesitates, I smack his ass. "Put them on. Give me a nice show."

He turns around and bends over--that's quite a show in and of itself--then steps into them and tugs them up. He tries in vain to keep them out of the crack of his very fine ass then gives up and just stands there. I can see the blush creeping down his neck.

"What are you waiting for? Turn around." I bite my knuckle to keep from snickering. When he finally does, I'm all business.

"Pretty," I murmur, my eyes fixed on his cock straining against the flimsy material. The head is popping up past the waistband, the balls drawn up tight in their delicate lace cage. I cross one leg over the other, squeezing my thighs together, pulling my jeans tight around my other surprise. The sight of him in my panties makes me a little dizzy and a lot hot.

I had a matching bra picked out but I decide to skip it. Something about his bare, hairy, muscular chest and those panties is so perfect. Instead, I throw him the stretchy, spaghetti-strapped sundress I know will accommodate his arms.

"Aw, man," he whines, but he puts it on. Luckily it's way too short on him so I can still see the panties and what's barely covered by them, which sort of makes up for the fact that it's too flowy. I really should have put more thought into the dress. It should have been one of those bandage things so I could see his hard-on through it.

Saving shoes for last, I get up and pull him into the bathroom. He flops down into the chair and I pick up the eyeliner but he plucks it away. "I'll do this, if you don't mind," he says with a huff. I don't mind at all. He does my makeup all the time and to be honest, he's much better at it than I'll ever be.

The wig is almost his limit but it'll look so good with his perfectly tasteful makeup that I can't let it slide. It's not even that ridiculous, just a simple black, shoulder-length thing with blunt bangs. I help him get it on straight and Jesus fucking Christ, it goes so well with his smoky eyes and plum lips. Placing my hands on his bare shoulders, I lean over and look at him in the mirror. "You look so fucking hot. I'm going to fuck you raw," I whisper. His pupils swallow up his gorgeous irises and I honestly don't know how long I'll be able to keep teasing him.

Back in the bedroom, I decide that I'd like thigh-highs with the shoes and he doesn't offer up any protest. With those words I uttered in the bathroom, he's willing to endure whatever I come up with as long as we get to the good part soon. In fact, as I smooth the stockings up his legs, he makes a sound that has me wanting to chuck the rest of my brilliant plan and get right to it. "Soon," I say, as much to him as to myself, and help him into the low heels he'd picked up for himself somewhere in anticipation of an audition that never happened.

I stand up and inspect the whole package. I twirl my finger and he turns awkwardly. I guess he never practiced with the heels. I can't hold back a snort.

"You just wait until next time," he says. "I'm gonna win and your ass is gonna be in a sling." His gruff voice is so incongruous with the way he looks, I have to laugh.

"That's what you always say. You need to shut up now though, because we're just getting to the best part." I take him by the wrist, pry his fist open, and press it to my crotch.

His mouth drops open and his eyes lock with mine. "Fuck me," he says, astonished.

"I fully intend to."

Sitting on the bed, I wait, watching him process what he just felt, what I just said, the whole scenario. I know I'm asking a lot and we never discussed this sort of thing so I'll be cool if he tells me to go fuck myself. He doesn't. He rolls his shoulders and tosses his head back, owning that shit right before my eyes, and gives me a coquettish smile.   "Now what?" he purrs.

"Walk for me," I say. "Over there and then come here." He does it so well, adding a little hip sway to his usual swagger, only stumbling once when he takes his first step. When he gets to the other side of the room, he looks over his shoulder saucily, making me want to go over there, shove him into the wall face first, and fuck that smirk off his face. I can't because there are other things I need more. I clutch the comforter in frustration.

"Get over here." My already deep voice sounds weird to me, more masculine than it ever has. He takes his sweet time, now knowing that the scales are tipping in his favor. Not for long, I think, wondering how this next part is going to go. I want to snap "On your knees" but I seem to have momentarily lost the ability to speak. I can only point to the floor at my feet but he does it.

"You look a little...uncomfortable," he says, sliding his hands up my thighs and undoing my jeans. I need to say something, get this back on the right track. He slips a hand into my fly and pulls my surprise into view. "Wow, " he breaths, licking his lips, and the only thing that comes out of my mouth is "Yuh."

My surprise is nothing major, something the patient woman at the sex shop assured me was good for noobs like the both of us, but it looks pretty impressive poking out of my jeans with his big hand wrapped around it. I'm ready to take control now but he fucks me up again.

"I bet you want me to suck it," he says, watching me through the fringe of his bangs. "I will but only if you tell me to."

This isn't going at all like I planned but really, what difference does it make at this point? "I do," I finally manage. I reach down, brushing the hair out of his eyes and tracing his lips. "Suck it. Suck my cock."

God, I wish it was real because he's seriously going for it. I'd give anything to be able to feel his mouth working my actual dick. At first his eyes are closed, his mascaraed lashes fluttering with the intensity of his sucking, and then he looks up at me, eyes glazed with lust. That must be how I look to him, I think, and then I can't think about anything but the two fingers he eases inside me and the thumb he's trying to sneak under my strap-on.

"Stop," I gasp, pushing his face away with the hand that had been cradling his scruffy jaw. Normally I need a little more than his fingers to come but I'm pretty close and I don't want to come yet.

"Wasn't it good?" he asks, looking up at me with those fucking eyes again, except the makeup makes it so much worse. I'm ready to call uncle and let him do whatever he wants. I don't know what made me think I was going to be running this show.

I flop back on the bed, laughing weakly. "It was awful. Make it up to me by letting me fuck you now," I say, trying to sound confident and asshole-ish.

There's a bit of rustling around and then the bed dips as he lies down next to me. The press of something cool in my hand startles me. It's a bottle of lube. I turn my head and he's grinning nervously at me. "How do you want it? This way or... " he asks, rolling over onto his stomach and flipping the dress up.

I could just do it. I was prepared to just do it but now... "You sure?" I ask, skimming my hand down his back, very aware of the tightness of his muscles. I stroke his ass, surprised again by how arousing it is to feel it encased in my panties. He spreads his thighs enough for me to slip my fingers lower.

"Yeah," he whispers. When my fingers brush his puckered bud, he sighs, relaxing and widening his legs a little more, letting the sensible heels thump to the floor. "But you have to be gentle. It's my first time," he adds, fluttering his lashes for effect.

I laugh but I'm freaking out a little. This is what I planned but I don't want to fuck it up. I don't want to hurt him. I don't want things to be weird afterwards.

"Hey," he says, touching my face. "You're thinking too much. Just go slow and do it. I want you to."

"Ok," I say, pushing him onto his back and kissing him. I can taste what's left of the lipstick on his lips and deeper than that, his excitement. I pull the dress over his head, careful not to dislodge the wig, and peel the panties off, tracing the pattern the lace left on his skin with shaky fingers.

"You're overdressed," he says, so I strip down, clumsy with nerves. He props himself up on his elbows and takes in the only thing I have left on: the black straps of the harness around my hips and thighs and the purple dick secured by an o-ring to the padded front hiding my pussy. He beckons and I go, my dick pressed against his as he hugs me close. I feel his heart speed up beneath my cheek and then he's handing me the lube again.

Sitting up, I flip the top and invert the bottle, but instead of pouring it into my hand, I drizzle it all over his cock.

"Little cold," he huffs, digging his fingers into the mattress.  

"Sorry, I'll just warm it up then..." I wrap my hand around him and pump, just the way he likes it: slow, tight, and with a little twist at the head. He throws his head back, the unnaturally shiny black strands of the wig fanning out on the pillow. His eyes are closed and his lipstick-smeared mouth is open, the tip of his tongue touching his upper lip in concentration. It's the perfect time.

As I inch my lube-slicked fingers lower, he goes still but he doesn't tense up like I would have. When he doesn't say anything, I keep going and then I'm there, circling the tight pucker, getting it nice and wet, making him writhe and moan. Watching him, I begin to work my finger in. My nails are freshly trimmed so there's no risk of hurting him that way but fuck he's tight. When I'm in to the first joint, he throws his arm over his face and drops his legs open a little more.

"Fuck," he says, his breathing gone ragged. I stop and begin to withdraw. "No! Keep going. I'm ok. I'm just...it's intense."

"Yeah," I say, going back to jacking his cock with my other hand. It helps so I figure going down on him can only make things better and shit, does it. His legs spread like butter and his hips jerk up and the next thing I know, I'm in to the second joint, which, according to my research, is right where I need to be. First I rub back and forth carefully, and then slowly, I curl my finger like I'm beckoning him, and there it is, the magic p-spot, round and smooth beneath my fingertip. He lets out a long, low moan that I can feel, and his cock pulses against my tongue.

"More," he rasps, bring his knees up to give me better access. I work another finger in, curling a little firmer and faster. One day, I'll make him come with my fingers but not tonight. I smile around his cock and then wince when the ruffling of my hair turns to tugging. "I'm ready, baby."

Withdrawing, I kneel between his legs and take up the lube again, slathering him with it, then using a handful on my pretty purple dick, fisting it slowly as I move closer.

"You want this?" I press the tip to his entrance, taking his hands and placing them behind his knees, making him open himself for me. He's quite a sight, buck naked except for the thigh-highs, on his back, practically begging for it.

He gives me the barest hint of a smile. "I do."

The time for talking and bullshitting is over. I sink into him, slowly, so slowly. Our earlier play and his horniness helps but we still have to stop a few times to let him get adjusted to having something a little bigger than my two fingers up his ass.

"You ok?"

His slightly furrowed brow and the way he's pressing his lips together seems to indicate that's he not but he takes my hands in his, squeezing gently. "I'm good. Just give me a few."

Staring into each other's eyes, we breathe together, deep and easy, and when he's ready, I let him rock his hips to take me the rest of the way in.

"Fu-uck," he groans when I start to move, and I wish more than anything that my dick was real and that I could feel him squeezing me like a hot, velvety glove. My movements are small and focused, my hips working in time to his open-mouthed panting. Soon, I'm panting along with him as each thrust smashes the base of the dildo against my clit. Now he's bucking against me and I have to wrap my arms around his thighs to keep my rhythm steady and the pressure where I want it.

The whole time we've been fucking, my eyes have been glued to his cock, which is as hard as I've ever seen it, so hard it almost looks painful and leaking pre-come into the tuft of hair above his navel. "I wish I could suck it," I murmur and he responds with an indrawn breath, craning his neck to look down at us and then dropping his head back, his eyelids drooping with pleasure. The twist I add to my next stroke makes him clutch my arms and then, with a hoarse cry, his back bows and he comes in powerful bursts, thick stripes of it painting his chest. There's even some on his face and in the wig. He sticks his tongue out to swipe some off of his lips and gives me a woozy grin.

Easing carefully out of him, I make my noodly-legged way to the bathroom and bring back a couple of warm, wet cloths to clean him up with.

"Let me," he says, kissing me sloppily, fumbling with the straps of my harness with one hand and trying to get at my sopping pussy with the other.

"Later." I give him a little shove and he slumps back, boneless and completely wrung out. I snuggle up next to him, petting his sweaty patch of chest hair, drifting pleasantly.

And planning my next prize.


End file.
